Voltammetric and physicochemical characterization of hydroxyl- and ether-functionalized onium bis(trifluoromethanesulfonyl)imide ionic liquids

Wu, Tzi‐Yi; Su, Shyh Gang; Lin, Keng-Fu; Lin, Yuan-Chung; Wang, H. Paul; Lin, Ming‐Wei; Gung, Shr-Tusen; Sun, I‐Wen

doi:10.1016/j.electacta.2011.06.051

Cited by 55 publications

(24 citation statements)

References 77 publications

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“…31 A study by Ganapatibhotla et al 49 of imidazolium ILs containing a long chain PEG monomethyl ether (7–16 oxygen atoms on average) demonstrated further that ether-functionalized ILs have lower viscosities than alkyl-substituted ones. The same viscosity reduction trend has been observed for ether-functionalized ILs based on other cations such as pyrrolidinium, piperidinium, oxazolidinium and morpholinium, 43, 44, 79, 80 ammonium and piperidinium, 39, 41, 81 phosphonium, 81, 82 as well as guanidinium. 45, 83, 84 Interestingly, guanidinium ILs containing an ester group have considerably higher viscosities than ether-grafted ILs (~300 vs .…”

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiosupporting

confidence: 77%

“…The hydroxyl groups likely form an intermolecular hydrogen-bond network contributing to the increased viscosity. 74, 79, 105 As pointed out by Ma et al 106 using femtosecond time-resolved depleted spontaneous emission, the hydroxyl groups in IL cations induce an enhancement of local microviscosity leading to slow solvation and rotation dynamics of the probe molecule rhodamine 700 in the ILs studied. In addition, the longer the hydroxyl-terminated PEG chain, the higher the IL viscosity due to stronger van der Waals interactions in addition to hydrogen bonding, such as examples in Table 1 including (in increasing order of viscosity): 63 < 64 < 65 , 66 < 67 < 68 , 69 < 70 < 71 .…”

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 90%

“…Pinkert et al 105 reported that hydroxyl-containing protic ammonium ILs of acetate or formate have conductivity values ranging from 4.8 × 10 –4 to 2.3 S/m at 5–75 °C, which suggests that their Walden products (molar conductivity × viscosity) are comparable to aprotic ILs. Interestingly, Wu et al 79 indicated that hydroxyl-functionalized pyrrolidinium and piperidinium ILs (with Tf 2 N − as anions) exhibit wider potential windows than those of corresponding ether-functionalized ILs.…”

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 99%

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Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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Section: Physicochemical Properties Of Ether- and Hydroxyl-functiosupporting

confidence: 77%

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 90%

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 99%

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Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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“…4 Among them, most investigations on ILs are related to imidazolium derivatives due to their low viscosity and high conductivity. Moreover, taskspecific ionic liquids (TSIL) are interesting materials for particular applications.…”

Section: And Solar Cellsmentioning

confidence: 99%

Influence of LiTFSI Addition on Conductivity, Diffusion Coefficient, Spin–Lattice Relaxation Times, and Chemical Shift of One-Dimensional NMR Spectroscopy in LiTFSI-Doped Dual-Functionalized Imidazolium-Based Ionic Liquids

Wang

et al. 2015

J. Chem. Eng. Data

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An ionic liquid (IL) 1-allyl-3-(2-methoxyethyl)imidazolium bis(trifluoromethylsulfonyl)imide ([AMO][TFSI]) is prepared, and the effect of the addition of LiTFSI into [AMO][TFSI] on the transport and physicochemical properties is studied herein. The diffusion coefficients of 1 H, 7 Li, and 19 F are determined using pulsed-gradient spin−echo NMR to study the dynamics of all ion species. The neat [AMO][TFSI] and LiTFSI-doped [AMO][TFSI] give approximately straight lines for the relationship of D vs Tη −1 , demonstrating that the Stokes−Einstein equation holds for the ionic diffusivity in the binary system. NMR T 1 relation time measurements show the 1 H-T 1 and 19 F-T 1 of LiTFSI-doped [AMO] [TFSI] decrease with the increase of Li salt concentration, which is due to the viscosity increases and the formation of stable coordination adducts of Li and TFSI when the salt concentration increases. From the study of chemical shift in one-dimensional NMR spectroscopy, an upfield shift in 1 H and 19 F spectra is observed in ILs with increasing lithium salt concentration; the formation of ion clusters is the dominant effect after the addition of LiTFSI in [AMO] [TFSI].

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“…The inherent properties of ILs such as high conductivity, a wide potential window, and air/moisture stability make them easy alternatives as chemically mild, stable electrolytes in the development of electrochemical and electrochromic (EC) devices [37][38][39][40]. In this work, we synthesized two series of 2,5-dithienylpyrrole-based conducting polymers (P(IND-co-perylene)s and P(MDOB-co-perylene)s) via electrochemical polymerizations.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical synthesis, characterization and electrochromic properties of indan and 1,3-benzodioxole-based poly(2,5-dithienylpyrrole) derivatives

Wu¹,

Liao²,

Chen³

2014

Electrochimica Acta

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Voltammetric and physicochemical characterization of hydroxyl- and ether-functionalized onium bis(trifluoromethanesulfonyl)imide ionic liquids

Cited by 55 publications

References 77 publications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Influence of LiTFSI Addition on Conductivity, Diffusion Coefficient, Spin–Lattice Relaxation Times, and Chemical Shift of One-Dimensional NMR Spectroscopy in LiTFSI-Doped Dual-Functionalized Imidazolium-Based Ionic Liquids

Electrochemical synthesis, characterization and electrochromic properties of indan and 1,3-benzodioxole-based poly(2,5-dithienylpyrrole) derivatives

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